[Remote] Director of Enterprise Sales

Note: The job is a remote job and is open to candidates in USA. The Difference Card is hiring a Director of Enterprise Sales to drive new business growth in the national large-group employer market. The role owns the enterprise sales cycle, sells TPA and provider quality scoring products, and leads a business development team while building partnerships with brokers, consultants, and enterprise decision-makers.

Responsibilities

• Drive Enterprise Sales Growth: Own full sales cycle for large employer groups from prospecting and discovery through negotiation and closing
• Build and Convert Pipeline: Independently source national enterprise opportunities while developing and converting referrals and leads from Sales Consultants and Marketing
• Team Leadership & Development: Lead, coach, and develop a team of Business Development Specialist, providing strategic direction, ongoing mentorship, and performance management to drive pipeline growth, achieve sales objectives, and foster a high-performing, results-driven team
• Sell Strategic Solutions: Position TPA services and PLUM products through consultative selling, aligning solutions with employer needs, benefit strategies, and cost management goals
• Develop Key Relationships: Build trusted partnerships with national brokers, consultants, C-suite executives, and benefit decision makers
• Lead Complex Sales Opportunities: Navigate lengthy sales cycles, multiple stakeholders, competitive evaluations, and contract negotiations
• Own Sales Performance: Manage pipeline activity, maintain accurate forecasts in Salesforce, and consistently deliver against revenue targets
• Partner & Influence: Collaborate across Sales, Marketing, and Client Success while sharing market insights to support enterprise growth strategies

Skills

• Bachelor's degree of equivalent combination of education and relevant experience
• 10+ years of sales experience in insurance, healthcare, employee benefits, or a related industry, with demonstrated enterprise sales success
• Proven ability to independently source, develop, and close complex deals with large employees (1,000+ employees)
• Experience selling insurance, TPA services, healthcare solutions, or healthcare point solutions into the enterprise market
• Strong understanding of employee benefits, employer sponsored health plans, and healthcare cost management
• Exceptional communication, presentation, negotiation, and relationship-building skills
• Established relationships with national brokers, consultants, or enterprise decision-makers
• Salesforce experience

Benefits

• Remote role, with a preference for candidates located in the Central U.S. region.
• Direct visibility and partnership with executive leadership.
• Opportunity to build and shape a high-growth enterprise sales channel.
• Comprehensive benefits package, including medical, dental, vision, and retirement offerings.
• The chance to make a measurable impact on company growth and long-term success.

Company Overview